This invention relates to the 2(1-vinyl-5-hexenyl)cyclopentanone having the structure: ##STR5## and the process for preparing same by reacting the ketal having the structure: ##STR6## with the unsaturated alcohol having the structure: ##STR7## and then heating the resulting intermediate and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes. This invention also relates to the novel intermediates having the structures: ##STR8##
Inexpensive minty, peppery, pineapple and jasmine aromas with natural oily and waxy undertones are highly desirable in the art of perfumery. Many of the natural materials (e.g., natural jasmine oil) which provide such fragrances and contribute such desired nuances are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products. Indeed, at times, jasmine oil itself has been impossible to obtain at any reasonable price.
In the course of the last five years, particularly, an increasing amount of attention has been devoted to the preparation and utilization of artificial perfumes and odor modifying agents possessing the aroma attributes of jasmine oil.
Cyclopentanone derivatives having jasmine undertones are known in the perfumery trade. Thus, "APRITONER" manufactured by Bedoukian Research Inc. of 21 Finane Drive, Danbury, Conn. 06810-4192 has the structure: ##STR9## and is described as having a "peach-apricot aroma with jasmine undertones".
Bortolin and Musco, Journal of Molecular Catalysis, Volume 22 (1984) pages 319-326 shows a synthesis which yields a very small amount of the compound having the structure: ##STR10## according to the reaction: ##STR11## whereby the major material produced in this reaction has the structure: ##STR12##
Nothing in the prior art, however, discloses an efficient process for producing the compound having the structure: ##STR13## or discloses the use in perfumery particularly as a jasmine substitute of the compound having the structure: ##STR14##